“Most artists are gamblers; they are impulsive people who don’t plan ahead.” This concept has been in the forefront of my mind for months now. The discovery was made in a conversation with my brother. We’ve seen this first hand in a few “serial entrepreneurs” that we’ve known. Start an idea, run with it for a little bit, and then let it drop or die off. Repeat.

I’ve done this myself.

I used to think this was a negative trait.

It’s not “having an unfinished idea” that is negative.
It’s not risk that is negative.
It’s not the notion of gambling that is negative.

In her book Big Magic, Elizabeth Gilbert speaks of a painter friend who also pointed out that most artists are gamblers. He made note of this on why art students get degrees. However, this can apply to any project or endeavour. He says,

Gambling is a dangerous habit. But whenever you make art, you’re always gambling. You’re rolling the dice on the slim odds that your investment of time, energy, and resources now might pay off later in a big way— that somebody might buy your work, and that you might become successful.

Elizabeth Gilbert continues this thought by saying…

You must be willing to take risks if you want to live a creative existence. But if you’re going to gamble, know that you are gambling.

…and finally…

And make certain that you can actually cover your bets (both emotionally and financially).

…and that was the missing piece of the puzzle.

Yes, it is gambling. That’s okay. Just make sure it is a sure bet. One that you can cover both emotionally and financially. If you are going to risk it all make sure that it is a thoughtful conscious decision to do so. Just don’t bet more than you’re willing to lose.